Substituted alkyl-hydroxydiphenyl methane



Patented Sept. 12, 19 33 pairs7$TA E 7' SUBSTITUTED ALKYL-HYDROXY- DIPHENYL METHANE Emil Klarmann, Jersey City, and Louis William Gates, Bloomfield, N. J., assignors to Lehn & Fink, Inc., Bloomfield, N. J., a corporation of Delaware No Drawing.

Application March 29, 1932 Serial No. 601,884

9 Claims. (01. 260-04) The present invention relates to certain hydroxy diphenyl methane derivatives having high bactericidal efficiency, and more particularly to chlorine methanes.

In accordance with the present-invention, we prepare chlorine substituted .alkyl hydroxy-diphenylmethanes, the chlorine-being substituted in either nucleus, and we have found such com 10 pounds to constitute highlyeff ective bactericidal agents.

hydroxyl groups are substituted in the same nucleus, the chlorine atom being substituted either 5 in this nucleus or in the other nucleus. Our

invention also includes homologues of such compounds in which a hydrocarbon radical is substituted in the methylene group containing the two nuclei. I r

0 The compounds, inaccordance with the present invention may be prepared, for example, by condensing benzyl chloride with an alkyl substituted phenol or phenolate, chlorinebeing substituted in either the nucleus oijthe benzyl chloride or 5 that of the phenol or phenolate. The condensation may be effected by direct reaction, particularly in the case of the use or a phenolate, or in the presence of a suitable condensing agent, such as zinc, zinc chloride, or the chlorides of other heavy metals or sulfuric acid. If desired, the condensation may be effected with compounds into which chlorine .has not been introduced, and the chlorination carriedout after condensation. I The following examples illustrate the production of compounds in accordance with the present invention.

The sodium compound of para-chloro-orthocresol is suspended in tolueneand treated with benzyl chloride in approximate equimolecular proportions, the latter being added slowly and withstirring to the former. The mixture is then heated moderately, say to 110 C. or thereabout, and stirred for a period of about 4 hours. a The reaction mixture is then treated with water and benzol to remove impurities soluble therein,-, and the desired phenolic bodies are then extracted with an alkaline methyl alcohol solution, precipitated by acidification; and subjected to -vacuum distillation The desired product, which is 5 chlor 3 methyl-2-hydroxy-diphenylmethane, distills between 172 and174 C. at 4.5 mm.

Hg pressure and melts. at 0. .Its phenol coefficient with respect to B. typhosus is'l6 and "with respect to StaphQaureus 243.

substituted alkyl-hydroXy-diphenyl j In the compounds prepared in accordance with the present invention, the'alkyl and insteadof cresols or cresolates.

position of. the substituting alkyl groups may be chloride 'and subsequently chlorinating the resulting product.

A further compound in accordance with the 0 present invention may be prepared by condensing, in'a similar manner, the sodium compound of para-chloro-meta-cresol with benzyl chloride.- The resulting product, which is'of an oily character and boils from 176 to 178 C. at 4.5 mm. 65, Hg pressure is, We believe, a mixture of 5-chloro- 4-methyl-2-hydroxy-diphenylmethane and 5- chloro-S-methyl-2-hydroxy-diphenylmethane. It has a high bactericidal value, particularly with regard to Staph. aureus. with respect to B. typhosus is 17.2, and with re-v spect to Staph. aureus is 403. V

In a similar manner, 4'-chloro-3 methyl-2-hydroxy diphenylmethane may be prepared by condensation of sodium ortho-cresolate with parachloro-benzyl chloride. -It boils at 167-172" C. at 4 mm. Hg and. melts at 48 C. The phenol coefiicient with respect to B. typhosus is 16, and with respect to Steph. aureus 243. By condensing para-'chloro-benzyl chloride with ortho-cresol in the presence of a chloride of a heavy metal,

such as zinochloride, l--chloro-3-methyl-4-hydroXy-diphenylmethane maybe prepared.

Corresponding ethyl, propyl, isopropyl, butyl and higher alkyl compounds may be prepared by '85. using the corresponding alkyl substituted phenols Changes in the effected by employing the meta or para-cresols or other meta or para-substituted alkyl phenols. 9

Chlorine may be substituted in either nucleus and we have found that the efiectiveness of compounds of this type against certain bacteria is unimpaired or may be improved by the substitution of additional halogens in either ring.

Weclaim:

1. As a composition of matter, a chlorine-sub:- stituted, mono-alkyl-hydroxy-diphenylmethane, the chlorine being substituted in a nucleus thereof, said compound having a high bactericidal ef- 2. A chlorine substituted mono-methyl-hydroxy-diphenylmethane, the chlorine being sub stituted' in a nucleus thereof, said compound having a high bactericidal eficiency. i

3. As a compositionof matter, an alkylhy- 'droXy-diphenylmethane having-a chlorine'substituted in the nucedus containing the substitut-"A ing hydroxyl group. 4. As a compositionof matter, a methyl-hy- Its phenol coefiicient 70 I tuted in the nucedus free from hydroxyl groups.

8. As a composition of matter, a. methyl-hydroxy-diphenylmethane having a, chlorine substituted in the nucleus free from substituting hydroxyl groups.

9. 4 chloro 3 methyl 4 hydroxy cli phenylmethane.

, EMIL KLARMANN.

LOUIS WILLIAM GATES. 

